Fe-SBA-15 catalyzed synthesis of 2-alkoxyimidazo[1,2-a]pyridines and screening of their in silico selectivity and binding affinity to biological targets

被引：19

作者：

Payra, Soumen ^{[1
]}

Saha, Arijit ^{[1
]}

Wu, Chia-Ming ^{[2
]}

Selvaratnam, Balaranjan ^{[2
]}

Dramstad, Thorn ^{[2
]}

Mahoney, Luther ^{[2
]}

Verma, Sant Kumar ^{[3
]}

Thareja, Suresh ^{[3
]}

Koodali, Ranjit ^{[2
]}

Banerjee, Subhash ^{[1
]}

机构：

[1] Guru Ghasidas Vishwavidyalaya, Dept Chem, Bilaspur 495009, Chhattisgarh, India

[2] Univ South Dakota, Dept Chem, Vermillion, SD 57069 USA

[3] Guru Ghasidas Vishwavidyalaya, Sch Pharmaceut Sci, Bilaspur 495009, Chhattisgarh, India

来源：

NEW JOURNAL OF CHEMISTRY | 2016年 / 40卷 / 11期

关键词：

POT MULTICOMPONENT SYNTHESIS; REGIOSELECTIVE SYNTHESIS; EFFICIENT CATALYST; PTP-1B INHIBITORS; COUPLING REACTION; DERIVATIVES; 2-AMINOPYRIDINES; NANOPARTICLES; DOCKING; IRON;

D O I：

10.1039/c6nj02134d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Here, we have demonstrated regioselective three-component synthesis of 2-alkoxyimidazopyridines using mesoporous Fe-SBA-15 as the catalyst and screened their in silico selectivity and binding affinity to different biological targets viz. farnesyl diphosphate synthase, phosphodiesterase III, GABAa and chemokine receptor CXCR4 using molecular docking simulations. Fe-SBA-15 has been characterized by nitrogen absorption-desorption, powder XRD, SEM, TEM studies and atomic absorption spectroscopic analysis. Fe-SBA-15 was very efficient in synthesizing imidazopyridines. The binding affinity study revealed that the 2-butoxy-3-(4-methoxyphenyl)-7-methylH-imidazo[1,2-a] pyridine (4g) moiety has exhibited even better affinity in terms of MolDock, re-rank and steric scores than the marketed anti-inflammatory drug, olprinone.

引用

页码：9753 / 9760

页数：8

共 83 条

[1] One-pot synthesis of imidazo[1,2-a]pyridines from benzyl halides or benzyl tosylates, 2-aminopyridines and isocyanides [J].

Adib, Mehdi ;

Sheikhi, Ehsan ;

Rezaei, Narjes .

TETRAHEDRON LETTERS, 2011, 52 (25) :3191-3194

[2] DERIVATIVES OF IMIDAZOLE .I. SYNTHESIS AND REACTIONS OF IMIDAZO[1,2-A]PYRIDIENES WITH ANALGESIC ANTIINFLAMMATORY ANTIPYRETIC AND ANTICONVULSANT ACTIVITY [J].

ALMIRANTE, L ;

POLO, L ;

MUGNAINI, A ;

PROVINCIALI, E ;

RUGARLI, P ;

BIANCOTTI, A ;

GAMBA, A ;

MURMANN, W .

JOURNAL OF MEDICINAL CHEMISTRY, 1965, 8 (03) :305-+

[3]

[Anonymous], 2012, MOLEGRO VIRTUAL DOCK

[4] BENZIMIDAZOLE CONDENSED RING-SYSTEM .9. POTENTIAL ANTINEOPLASTICS - NEW SYNTHESIS OF SOME PYRIDO[1,2-A]BENZIMIDAZOLES AND RELATED DERIVATIVES [J].

BADAWEY, E ;

KAPPE, T .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1995, 30 (04) :327-332

[5]

Bae J.S., 2007, [No title captured], Patent No. [WO 2007011163 A1, 2007011163, 2007011163A1]

[6] Copper-Catalyzed Synthesis of Imidazo[1,2-a]pyridines through Tandem Imine Formation-Oxidative Cyclization under Ambient Air: One-Step Synthesis of Zolimidine on a Gram-Scale [J].

Bagdi, Avik Kumar ;

Rahman, Matiur ;

Santra, Sougata ;

Majee, Adinath ;

Hajra, Alakananda .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (09) :1741-1747

[7] The remarkable catalytic activity of ultra-small free-CeO2 nanoparticles in selective carbon-carbon bond formation reactions in water at room temperature [J].

Banerjee, Subhash .

NEW JOURNAL OF CHEMISTRY, 2015, 39 (07) :5350-5353

[8] ZnO nanoparticles: a green efficient catalyst for the room temperature synthesis of biologically active 2-aryl-1,3-benzothiazole and 1,3-benzoxazole derivatives [J].

Banerjee, Subhash ;

Payra, Soumen ;

Saha, Arijit ;

Sereda, Grigoriy .

TETRAHEDRON LETTERS, 2014, 55 (40) :5515-5520

[9] Free-ZnO nanoparticles: a mild, efficient and reusable catalyst for the one-pot multicomponent synthesis of tetrahydrobenzo[b]pyran and dihydropyrimidone derivatives [J].

Banerjee, Subhash ;

Saha, Arijit .

NEW JOURNAL OF CHEMISTRY, 2013, 37 (12) :4170-4175

[10] A green one-pot multicomponent synthesis of 4H-pyrans and polysubstituted aniline derivatives of biological, pharmacological, and optical applications using silica nanoparticles as reusable catalyst [J].

Banerjee, Subhash ;

Horn, Alissa ;

Khatri, Hari ;

Sereda, Grigoriy .

TETRAHEDRON LETTERS, 2011, 52 (16) :1878-1881

← 1 2 3 4 5 6 7 8 9 →